DE1301555B - Verfahren zur Herstellung von hochmolekularen Poly-[1, 4-bis-(hydroxymethyl)-cyclohexan-terephthalat] - Google Patents
Verfahren zur Herstellung von hochmolekularen Poly-[1, 4-bis-(hydroxymethyl)-cyclohexan-terephthalat]Info
- Publication number
- DE1301555B DE1301555B DEC38261A DEC0038261A DE1301555B DE 1301555 B DE1301555 B DE 1301555B DE C38261 A DEC38261 A DE C38261A DE C0038261 A DEC0038261 A DE C0038261A DE 1301555 B DE1301555 B DE 1301555B
- Authority
- DE
- Germany
- Prior art keywords
- bis
- hydroxymethyl
- production
- terephthalate
- molecular weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000010936 titanium Substances 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- -1 alkyl radical Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- KKSAZXGYGLKVSV-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO KKSAZXGYGLKVSV-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010036 direct spinning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC38261A DE1301555B (de) | 1966-02-18 | 1966-02-18 | Verfahren zur Herstellung von hochmolekularen Poly-[1, 4-bis-(hydroxymethyl)-cyclohexan-terephthalat] |
| US606333A US3493542A (en) | 1966-02-18 | 1966-12-30 | Method for the preparation of poly-(1,4 - bis - (hydroxymethyl)-cyclohexane-terephthalate) |
| FR93927A FR1517915A (fr) | 1966-02-18 | 1967-02-07 | Procédé de préparation de poly-(1, 4-bis-(hydroxyméthyl)-cyclohexane-téréphtalate) |
| GB7687/67A GB1170843A (en) | 1966-02-18 | 1967-02-17 | Process for the Production of Poly-(1,4-bis-(hydroxymethyl) cyclohexane terephthalate |
| BE694242D BE694242A (cs) | 1966-02-18 | 1967-02-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC38261A DE1301555B (de) | 1966-02-18 | 1966-02-18 | Verfahren zur Herstellung von hochmolekularen Poly-[1, 4-bis-(hydroxymethyl)-cyclohexan-terephthalat] |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1301555B true DE1301555B (de) | 1969-08-21 |
Family
ID=7023208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC38261A Pending DE1301555B (de) | 1966-02-18 | 1966-02-18 | Verfahren zur Herstellung von hochmolekularen Poly-[1, 4-bis-(hydroxymethyl)-cyclohexan-terephthalat] |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3493542A (cs) |
| BE (1) | BE694242A (cs) |
| DE (1) | DE1301555B (cs) |
| FR (1) | FR1517915A (cs) |
| GB (1) | GB1170843A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5106944A (en) * | 1990-07-03 | 1992-04-21 | Eastman Kodak Company | Process and catalyst-inhibitor systems for preparing poly(1,4-cyclohexenedimethylene terephthalate) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2901466A (en) * | 1955-12-22 | 1959-08-25 | Eastman Kodak Co | Linear polyesters and polyester-amides from 1,4-cyclohexanedimethanol |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053809A (en) * | 1958-04-15 | 1962-09-11 | Celanese Corp | Phosphine-metal compound catalyst |
| US2989499A (en) * | 1958-04-15 | 1961-06-20 | Celanese Corp | Process employing catalyst |
-
1966
- 1966-02-18 DE DEC38261A patent/DE1301555B/de active Pending
- 1966-12-30 US US606333A patent/US3493542A/en not_active Expired - Lifetime
-
1967
- 1967-02-07 FR FR93927A patent/FR1517915A/fr not_active Expired
- 1967-02-17 BE BE694242D patent/BE694242A/xx unknown
- 1967-02-17 GB GB7687/67A patent/GB1170843A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2901466A (en) * | 1955-12-22 | 1959-08-25 | Eastman Kodak Co | Linear polyesters and polyester-amides from 1,4-cyclohexanedimethanol |
Also Published As
| Publication number | Publication date |
|---|---|
| US3493542A (en) | 1970-02-03 |
| FR1517915A (fr) | 1968-03-22 |
| BE694242A (cs) | 1967-07-31 |
| GB1170843A (en) | 1969-11-19 |
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